


My Pretty Sammy Baby

by glowystars325



Category: Supernatural
Genre: Bottom Sam Winchester, Dirty Talk, Feminization, First Time, Lingerie, M/M, Multiple Orgasms, Sex Toys, Top Dean Winchester
Language: English
Status: Completed
Published: 2021-02-05
Updated: 2021-02-05
Packaged: 2021-03-16 17:42:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,236
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29211315
Author URL: https://archiveofourown.org/users/glowystars325/pseuds/glowystars325
Summary: Sam wanted to unwind, but Dean pulls him away and catches Sam in a different getup when his little brother gets desperate for relief.
Relationships: Dean Winchester/Sam Winchester
Comments: 2
Kudos: 182





	My Pretty Sammy Baby

Sam slowly relaxed into the armchair, book in his hands. He needed this, teasing himself for days. Sam never got to plan like this, get himself worked up with all the stops, all of his biggest turn ons. Lingerie, jeweled plug and his cage on, all to tease himself, drive himself crazy before riding his squirting vibrator. All thanks to a slasher flick marathon Dean had been excited for, bringing it up constantly for a week. 

The right junk food, a quiet week, and a brand new erotic novel, all the things to keep both brothers happy. He eagerly opened the book and started to read, dying to get to the good part as the two men flirted and fought and finally went on a date.

He bit his lip, reading the scene and he couldn't help but wiggle on the plug inside of him, so close to his prostate. The silk of his bra and panties hidden carefully under his layers turned him on more as the men started to rub against each other. He wanted to get hard, mouth watering at the image, picturing _ Dean _ on top, growling in his ear. He let out a tiny whimper and squeezed his lace topped thighs together. 

"Dude you seem  _ weirdly _ into that book. Lesbians?" He almost jumped out of the chair, but quickly caught his composure.

"Huh? Just a… good plot point. Not your thing," he carefully marked the page and closed the book, soft grey cover tucked into his shirt, "What's up?

"Okay then," Dean looked at him with his almost laser eyes that Sam always struggled to not squirm under, "Get in the car. I already grabbed your duffle."

"Can I have a minute? Just change into something different?"  _ Nonono. Dean would crucify him. _ He tried not to panic, tried to figure out how to hide… well, everything. Dean was going to find out, he always figured out Sam’s secrets, especially when it was prime embarrassment material.

"We don't have time, Samantha. Get your ass in the car. Leave the book because I need you on research during the drive."

“But I want to-” Sam started, but his brother cut him off with a look.

“Dude. Ass in car, work to do.”

“I want to change!” He sounded whiney to his own ears, like a snotty ten year old little brother that wanted a second cookie. Of course Dean snorted and gave him the “I’m older and know better” look, “Five minutes.”

“Then drop the pants, Samantha. Need to change, strip on the way and get dressed in the car. Need to paint your nails too?”

“Fine. You’re such a jerk.”

“And you’re acting like a bitch. I definitely think the case is a spook, so, start running history.” Dean ordered as they got in the impala, engine roaring to life.

“So, what info do you have?” he wanted to sigh and kick up a fight, still feeling needy and horny, half his brain still focused on his fantasies.

Sam typed out the password on his laptop as they hit the highway, Dean speeding towards Kansas City, listening to Dean explain the case. “Three dead, all the same way, locked rooms and frost on the windows. And frost ain’t a thing in August.”

“Vengeful spirit. Got it,” fingers double clicked on the chrome icon, “Did you already find a connection between the-” Sam trailed off and swallowed at the porn on the screen. High skirt, hanging balls and Sam’s mouth was watering when the moans came through the speaker. 

Dean quickly hit the mute button and looked firmly at the road, “Wanted something different. Don’t be weird about it.”

“It’s cool,” he tried to sound calm, wanting to be the man on screen, getting fucked roughly by the hard cock, “Don’t use my laptop for porn.” Old, but it was something he was supposed to say. Sam closed the tab, a silent thanks for Dean not knowing what incognito was, because Sam  _ needed _ to finish that video.

“Yeah, well don’t forget that I know about your weird hair thing. So don’t bring it up again.”

“Liking my hair being pulled isn’t weird,” protests felt useless as ACDC started blasting in the car. Tiny shake of the head and his focus was back on the case, well as much as he could focus on it. Hours passed, them talking shop, connecting victims from old articles.

“We can get out and stretch soon.”

He could only manage a nonverbal grunt. Sam felt like he was dying, plug rubbing him constantly. The lace bra was starting to rub his nipples to the point of being almost uncomfortable and his dick was still stuck in the cock cage, a blessing in disguise at this point.

"Are you feeling okay, bro? You're kinda red."

"I'm fine. How much longer till we can get to the motel?"

"About 15 minutes. I wanna get food first."

"Can't we just order a pizza?"

"Stop being whiny, Samantha. Pizza actually sounds good, but I want to sit down and make a game plan."

“Please?”

“Fine. Motel first and I’ll order pizza.” Dean caved the second he saw the puppy dog eyes, “Put them away, and I’ll even order a veggie pizza.” The smile was with picking off mushrooms.

“Thank you.”

“Yeah yeah. Shut up.”

After pulling in and getting a room, Sam felt only slightly more relaxed, but he still wasn’t in the clear. Dean was predictable. Bags, check sheets, once over then-

"Getting ice,” his brother didn’t wait for a response. 

The second the door shut, Sam grabbed his kit and went to the bathroom, shutting the broken lock door. It was all too much. The plug in for too long. Three days in his cock cage was the longest Sam's ever done to himself and he  _ needed _ to get a release. "Oh God. Uhhgh," he got out of his jacket and shirts, thighs and ass clenching with need. Sam needed his vibrator, needed out of the cage, needed to cum.

Bending over was cruel to himself as he finally caught his breath long enough to get out of his jeans, taking shaky breaths before he could get himself free. 

"Sam, I have to- holy shit," Dean cut himself off, staring at his little brother's get up in the bathroom, lock picking kit on the grimy counter top. Sam's long legs had white stockings crawling up past his knees and to his mid thighs where a pastel pink garter belt held them up. A pretty pink bra was sheer, hard nipples peeking through the delicate lace. Green eyes finally landed on the lacy and silk panties, completing the entire look. His mouth watered and he couldn't help but stare at the bulge straining the fabric. "Been wearing this all day?" Dean couldn't pull his eyes away.

"I-I. Dean?"

"Now, I have a few questions. But the one I'm most curious to ask is, why the lock pick?"

"You can still pretend you didn't see anything. I'm sorry," Sam was close to tears, humiliation burning in his throat.

"No freaking way," his voice was low and gravely. He crowded Sam closer to the counter, keeping himself from touching. "Fuck. You bitch, Sam. One thing teasing me all these years, but now you're wearing these pretty things. How am I supposed to forget this sexy thing?"

"Please don't make fun of me. I'm sorry!"

Dean shook his head, "Don't be sorry, sweetie. You look so pretty." He was close, barely fighting his own urges, "Don't even worry about it. God. The things I want to do right now." Sam let out a whimper that made him groan, "Shit. Don't make noises like that. Tell me you don't want this Sam. Tell me you don't want me to touch you."

"You want to touch me?" Sam's voice was small.

"Years," he bit his lip, closing his eyes, knuckles white on the countertop, "Tell me no."

"What if I don't want to tell you no?"

"You can't mean that. Fuck!" Dean forced himself away, staring up at the ceiling, focusing on a water stain. "Fuck. Fuck. Okay, Sammy. If you're _ sure  _ you want this, go lay on the bed for me. I'm going to go to the bathroom. If you don't want this, get dressed and I won't bring it up again. I'm not going to force you to do anything. And I'll understand completely."

He finished, trying to listen for the zipping of a duffle bag as he washed his hands.  _ Sammy deserves you being nice and clean. _ Dean grabbed an old washcloth and carefully cleaned himself, getting rid of the day's sweat. It was half stall, half hope on his part, but he tucked his half hard erection back away, just in case he missed Sam leaving.

Dean's unease lifted the second he opened the bathroom door, looking at Sam sprawled out on the bed, arms raised on the pillows and legs open for him, "Like this, De'?"

"Jesus Christ, you could kill a guy with a sight like that," he pushed off his jacket, mouth watering. Green eyes went up and down with the curves and sharp muscles, “Pink is such a pretty color on you, baby.”

“Are you going to join me or just keep staring?” 

“Definitely joining,” Dean stripped bare as his mouth explored Sam's, each kiss feeling like a victory he's craved since his first wet dream. Both of their hands wandered, Sam's needy, desperate, restless. Dean's took their time, playing with soft hair that was just slightly greasy, brushing against the long neck with his fingertips, rubbing the hard chest and the smoothness of high quality lace. But for as hard as Dean was, he didn't feel Sam grow, didn't feel a hot erection. 

He pulled back just enough to look at Sam, check for insecurities or doubts. "Obviously I'm not doing my job right if you aren't hard yet," he tried to joke, but it was a weak attempt. Dean kissed his cheek, "Baby if you don't want this, tell me. I won't be upset."

"I want you so much," Sam kissed him hard, whining when he jolted the plug again, "Fuck me De'." He needed Dean to know how desperate he was for this, how much he wished and dreamed just for his brother to kiss him.

"You aren't even hard-"

"Can't."

"What?" His hand rubbed him and he tilted his head with a question before going under the fabric and he bit Sam's lip, "You kinky little thing," he growled out, fingers brushing the stainless steel rings around his soft cock and Sam moaned, wanting to cum in his panties. 

Dean rubbed his aching balls and his little brother threw his head back, "Dean! Ohh. Mhhhh. Too much. More." 

He gave a gentle squeeze as he smirked, “How long have you been wearing this, baby?”

“Days. Three. Fuck, hands are so big, De’. Feels good. Need more.”

"Is that what I think it is?" His fingers rubbed against something hard and he cursed, "Fuck. Fuck baby. You're trying to kill me. I have to see you. Mhhh," he sucked on the nipple through the lace, "Wearing all this. So pretty like a present. My pretty little girl."

"Dean please!! Need you to touch me. Finger me." Hands were back on his chest and Dean pulled the bra off in a well practiced move, another kiss on his lips, softer this time.

“Have any lube, Sammy baby? Want your pussy nice and wet for me.” Sam let out a long whine and nodded eagerly.

“Side pocket of my bag. Hurry. Need you.” Heat left and was filled with the cold ac and both of them just wanted to be back in each other's space, breathing in their brother’s air.

The bed dipped and a hot mouth went over his panties, “Mmhm, Dean feels good, his hand grabbed what he could of the soft hair, rubbing the back of his head. Calloused hands rubbed his hips before tugging away the thin layer between them, Sam helping him take the panties off, kicking them aside.

“Oh fuck. Let me see that plug,” fingers coaxed his thighs wider. A low groan of appreciation escaped his lips, looking at the shining green jewel that matched Dean’s eyes exactly, “Buy this thinking of me?” he started playing with it, pulling a tiny bit out before pushing it back in, over and over. His little brother was panting with need, balls heavy.

“Yes. Matches your eyes always think about you when it’s in me,” he confessed, whining when it was removed. “No, want to be full.” His protests turned into a happy whine when two wet fingers rubbed against his hole before pushing in, “Better, so much better,” he babbled, Need your cock, De’. Need you to fuck me.”

“Yeah? How’s this?” a third finger pressed in and Dean rubbed his prostate, stroking it in tiny motions before pressing harder on a push in.

Sam’s hips jolted up as he screamed his name, legs quaking with a dry orgasm. Dean didn’t expect to be shoved forward by thighs and hands losing control and just needing Dean that much closer. “Fuck, Dean! Need to cum. Let me out. Please. Wanna cum too. Feels so fucking good.”

"Holy shit. That was beautiful, Sammy. Jesus. You’re so fucking pretty. I'm being nice, baby girl. I'll let you out of your cage, but you can't cum till I say." Sam nodded, head dizzy with need. Dean quickly picked the tiny lock and pulled the cage off, Sam whining with relief. He watched his little brother get hard instantly as Dean nibbled on his thighs and slowly removed the stockings. "God, you're so pretty, Sammy." Once he was completely naked, he kissed back up, pausing to suck on the leaking head for a second. He was rewarded with a high pitched " _ Dean!" _

He couldn't help but grin as he pulled away from the leaking tip and started sucking on the dusty nipple, pinning Sam's twitching hands to the pillow.

Sam moaned loudly, "Dean! Nonono. Gonna cum. Wanna be good." He struggled with the weight on his wrists desperately wanting to cut off the orgasm starting to spill over, tip almost purple and leaking precum in rivers. Tears sprung to his eyes, not wanting to disappoint him so fast after being let out of his cage. "Can't stop it. Wanna be good. Please nonono. Feels too good!"

"Shhhh. It's okay, baby. Cum Sammy. Cum for me, want to see you."

"Dean! Ohhhh.. mhhhmmm," he forced his lips onto his brother's cum soaking between them. He was panting, still hard from the three days without. Dean kissed him slowly, one hand in his hair and the other still on his wrists. Swallowing every whimper and whine as Sam came down from his high.

"Jesus Christ. You're better than I ever dreamed. Haven't even started yet and you're this pretty. My perfect baby doll."

“Need more, De’,” he whimpered at the first tease of Dean’s slick cock at his entrance.

"Ready for my cock, Sammy?" He nodded, “Then beg for it.”

"Yes! Yesyesyes. Ohhh," his wiggled trying to push against the mushroom head Dean was teasing him with, "Dean please. Need you. Need it. Plea-ah!!" His eyes rolled to the back of his head as he pushed in. His mouth was open wide back arching up and Dean couldn’t remember doing anything good enough to deserve such a beautiful sight.

"Plugged up all day and still so freakin tight. Better than a pussy baby." He was panting, struggling to keep his composure. Tight hot heat, Sam’s moans, and his best fantasy coming to life all had him ready to shoot off, “Shit, Sammy. So good. Ready? Please tell me i can move.”

Sam nodded eagerly, "Please. Make me feel good De'. Ohhh. It's so big. Please. Please." 

He started to move, slowly pulling out and pushing more of him in, "Big huh? Not even in all the way. Feel good Sammy?"

"Yes! Oh. Ohgod. Mhhh," he sucked on Dean's thumb, close enough to his lips and whined. "More?"

"Jesus," Dean pressed his thumb back in Sam's mouth, hips started to move faster. His long legs wrapped around him, urging him to move harder and faster as the air around them, “You’re pure fucking sin. Oh, oh. Fuck baby.” Rhythmic slaps of skin was a steady metronome of both of their moans, Dean’s slipping dirty tongue, Sam’s pretty mouth begging.

“Dean deandean,” Sam grew louder and his legs were pushed up over the scared and strong shoulders, “DEAN!” the new angle had him seeing stars.

“Did I hit that sweet spot just right baby?” Dean did it again, not missing now that he knew exactly where to aim. Sam was a mess, moaning and whimpering. It sounded better than any Zeppelin song to exist, better than anyone else he ever slept with and he would never get enough of it.

His hips moved faster, hand going to fist the long hair, each tug making Sam clench around him and Dean was barreling straight into his orgasm. “Cum for me baby brother.”

Sam tightened up like a pulled back bow, high pitched breath turned into a stretched out, “ _ Deeaannn, _ ” cum splashing hot on Dean’s stomach and his, burn and tightness like a vice around him had Dean filling him with hot cum, painting his hole white as their lips crashed back together.

Dean collapsed on him, hips twitching from the aftershocks. "Best lay ever. Mhhnn love you Sammy. So much." He pet his long hair, crazy from the pillows.

"I love you too."

Their lips met in a tender kiss, "Let me get a washcloth and get you clean."

Dean was fast, gentle hands cleaning Sam’s chest, abs, oversensitive cock, his thighs, and finally over his hole, wiping both of their cum away, “What’s going on in that head of yours?” he asked before cleaning himself.

"This isn't a one time thing, right?" Sam looked up with big eyes as Dean finished wiping away the tacky cum in his treasure trail, "I've wanted this for so long and I know the… it's a lot and. I'm a freak. I can be normal."

"Excuse me? Don't talk shit about my little brother. That's how you get your ass kicked."

"Dean." His brother gave him a soft smile and tossed the cloth before crawling into bed. "I'm-"

"I know baby. You're being serious. Not a one time thing, trust me. I ain't ever letting you go. You're my mine all mine. And I might actually cry if you never wear panties again. You are so pretty in them, not that you aren’t before. Just, they’re a little scoop of ice cream with a nice hot apple pie, and not just a slice."

"Really?"

"Promise. If you're freaky, then so am I. And you’re so beautiful, Sammy. Good first time?"

"Yeah," Sam closed his eyes and nuzzled into his shoulder, "Really good. Wish I got to suck you. But still really good." 

Dean's jaw dropped, "You're better than all my wet dreams ever. I'll definitely let you do that whenever you want. But let's sleep now, baby. Nap, food, my pretty Sammy baby." He pulled Sam even closer, legs tangled and arms tight around his baby brother as they both drifted off into an easy sleep.


End file.
